Cyanidin-3-O-sophoroside chloride 98% Purity Natural Product Reference Standard CAS 38820-68-7 Research Grade Anthocyanin

Product Overview

Cyanidin-3-O-sophoroside chloride is a naturally occurring anthocyanin pigment belonging to the class of anthocyanidin-3-O-glycosides. It consists of the cyanidin aglycone (2-(3,4-dihydroxyphenyl)chromenylium core) glycosylated with a sophoroside moiety at the 3-position. Sophorose is a disaccharide composed of two β-D-glucose units linked by a β-1,2-glycosidic bond .

With the molecular formula C₂₇H₃₁ClO₁₆ and a molecular weight of 646.98 g/mol (or 647.05 g/mol), this compound appears as a dark red to purple-red powder . It exhibits characteristic UV-Vis absorption with λmax at approximately 526 nm in methanol containing 0.1% HCl, with a molar extinction coefficient of 31,600 ± 2,800, making it easily identifiable and quantifiable by spectroscopic methods .

Natural Sources

Cyanidin-3-O-sophoroside has been identified in various plant sources:

• Black peanut skins (Arachis hypogaea L.): One of the two most abundant anthocyanins, with a content of 5.77 ± 0.42 mg per 2 g dry black peanut skins 

• Red raspberries (Rubus idaeus): Present as a significant anthocyanin component 

• Hibiscus flowers (Hibiscus sabdariffa): Characteristic anthocyanin compound 

• Purple potato (Solanum tuberosum): Present as acylated derivatives 

• Blackcurrant (Ribes nigrum): Present but delphinidin derivatives are dominant 

• Other sources: Erythrina excelsa, Cornus species, and various berries 

Biosynthetic Pathway

The biosynthesis of cyanidin-3-O-sophoroside is a multi-step enzymatic process :

1. The pathway begins with the amino acid L-phenylalanine, which is converted to p-coumaroyl-CoA through a series of core enzymes including PAL, C4H, and 4CL 

2. Chalcone synthase (CHS) catalyzes the condensation of p-coumaroyl-CoA with three molecules of malonyl-CoA to form naringenin chalcone 

3. Chalcone isomerase (CHI) converts naringenin chalcone to naringenin 

4. A series of hydroxylation and reduction steps (F3H, F3'H, DFR) produce leucocyanidin 

5. Anthocyanidin synthase (ANS) oxidizes leucocyanidin to the unstable cyanidin aglycone 

6. UDP-glucose:flavonoid 3-O-glucosyltransferase (UF3GT) attaches a glucose molecule to the 3-hydroxyl position, forming cyanidin-3-O-glucoside 

7. A specific glucosyltransferase (UDP-glucose:anthocyanidin 3-O-glucoside-2''-O-glucosyltransferase) adds a second glucose molecule to form the sophoroside moiety 

Extraction and Purification

For isolation of Cyanidin-3-O-sophoroside with high purity (>97%), combined column chromatography is typically employed :

1. Extraction: Acidified methanol or ethanol extraction from plant material (e.g., black peanut skins)

2. Purification: Combined column chromatography technique

3. Yield: From 2 g dry black peanut skins, approximately 5.77 ± 0.42 mg of cyanidin-3-O-sophoroside can be obtained with purity of 97.29% by HPLC-PDA 

Mechanism of Action & Biological Activities

Research has demonstrated several biological activities of cyanidin-3-O-sophoroside :

• Neuroprotective Effects: In an AlCl₃-induced zebrafish model of Alzheimer's disease, cyanidin-3-O-sophoroside (C3S) demonstrated neuroprotective properties, including:

  • Amelioration of locomotor impairments

  • Suppression of acetylcholinesterase (AChE) activity

  • Decreased brain oxidative stress levels

  • Upregulation of AD-related gene expression

  • Mitigation of brain tissue pathological changes

• Robust Binding Affinity: Molecular docking and dynamics simulations indicated that cyanidin-3-O-sophoroside exhibits robust binding affinity and stable binding to AChE, a crucial therapeutic target for Alzheimer's disease 

• Antioxidant Activity: As an anthocyanin, it scavenges free radicals through electron donation by multiple hydroxyl groups

Research Applications

• Phytochemical Analysis: Serves as a reference standard for HPLC and LC-MS analysis of anthocyanin-containing plant extracts, particularly for quality control of berry products and black peanut skin extracts

• Food Chemistry: Reference standard for anthocyanin analysis in food products and beverages

• Quality Control: Acts as a marker compound for anthocyanin-rich botanical extracts (red raspberry, hibiscus, black peanut)

• Pharmacological Research: Used in studies investigating neuroprotective, antioxidant, and anti-inflammatory activities

• Natural Colorant Research: Used in the development of natural food colorants

Quality Specifications

• Purity: ≥98.0% determined by HPLC (area normalization) 

• Appearance: Dark red to purple-red powder 

• Identification: Confirmed by UV-Vis (λmax ~526 nm) and MS spectral matching 

• Molecular Formula: C₂₇H₃₁ClO₁₆ 

• Molecular Weight: 646.98 g/mol 

• Molar Extinction Coefficient: 31,600 ± 2,800 at 526 nm in methanol + 0.1% HCl 

• Water Content: ≤5.0% (Karl Fischer) 

• Each batch accompanied by comprehensive Certificate of Analysis (COA) with HPLC chromatogram 

Packaging & Storage

Packaging Options:

• 5mg, 10mg, 25mg, 50mg, 100mg, 500mg, 1g amber glass vials 

• Custom packaging available upon request

Storage Conditions :

• Long-term: Below -15°C (e.g., -20°C), in sealed containers, protected from light and moisture 

• Short-term: 4°C, in sealed containers (stable for up to 2 years)

• Powder form: Stable for up to 3 years at -20°C

• In solvent: Stable for up to 6 months at -80°C, or 1 month at -20°C 

• Equilibration: Allow product to equilibrate to room temperature before opening

• Shipping: Shipped with ice pack (cold chain) for stability; stable at ambient temperature for a few days during ordinary shipping 

Safety Information

This product is intended exclusively for research purposes, including content determination, identification, pharmacological experiments, and bioactivity screening . It is not for human use, clinical diagnosis, or therapeutic applications. Standard laboratory safety practices, including appropriate personal protective equipment, should be followed when handling this compound .

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